Ethanol → 2-(5-phenylpentyl)pyrido[2,3-d]pyrimidin-4(3H)-one

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Reaction Steps

To 6-phenyl-hexanoic acid (3-cyano-pyridin-2-yl)-amide (360 mg, 1.2 mmol) in sodium hydroxide (6 ml, 5M) was added ethanol (0.1 ml) and hydrogen peroxide (3% in H2O, 1.5 ml). The reaction mixture was heated to reflux for 3 hours. Water was added, the solution was acidified (pH 5) and extracted with EtOAc (3 times). The combined organic phases were washed with brine, dried over Na2SO4, filtrated and concentrated in vacuo. Column chromatography on silica gel with CH2Cl2:MeOH 9:1 as eluent, followed by trituration from diethyl ether yielded 2-(5-phenyl-pentyl)-3H-pyrido[2,3-d]pyrimidin-4-one as a white solid, MS (m/e): 294.3 [M+H+].

Provenance & Evidence